Oct 31, 2020 · 26m · top-founders
Todoist Productivity Tool Hits $14m Revenue, Bootstrapped
Amir Salihefendić · 13m spoken Nathan Latka · 7m spoken Frank Bien · 4s spoken Eric Yuan · 4s spoken Vivek Bhaskaran · 2s spoken
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
Nathan Latka interviews Doist founder and CEO Amir Salihefendić on how he bootstrapped productivity software Todoist and Twist to more than fourteen million dollars in annual recurring revenue. Amir shares his unconventional perspectives on SaaS pricing, remote organizational structure, metric tracking, and maintaining long-term independence.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Nathan holds 36% of the talking time here. How this is scored →
Nathan as informed peer 5.1 Guest teaching 3.7 Guest disagreement 4.1 Nathan pushing back 4.7
speaking balance: gold is Nathan, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 23:14 Defiant rejection of acquisition offers
Amir responds with 'fuck you' to the hypothetical idea of selling the company for $200 million cash, asserting he refuses to even open buyout emails.
Hardest push from Nathan ▶ 20:49 Host confronts founder on customer churnNathan aggressively challenges Amir's detachment from metrics, asking if customer churn upsets him since losing users equates to people 'killing your baby'.
Biggest teaching moment ▶ 21:06 Guest redefines startup stress with zen philosophyAmir reframes Nathan's anxiety around churn metrics by outlining a zen approach to software building, noting that users should move on if the tool does not fit.
Nathan holds their own ▶ 19:48 Host deduces churn rate from unit economicsNathan instantly calculates customer lifespan and deduces an annual churn rate near 70% using Amir's stated $100 LTV and $5 monthly pricing.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Nathan as informed peer | Guest teaching | Guest disagreement | Nathan pushing back | Why |
|---|---|---|---|---|---|---|
| Todoist Origin Story and First Paying Customers | 4 | 3 | 1 | 2 | Nathan digs into the timeline from 2007 to 2010 when Amir ran a social network alongside Todoist. Amir candidly explains how his early blog helped attract the first paying users to cover server costs. | |
| Freemium Pricing Mechanics and Business Tier | 5 | 3 | 2 | 4 | Nathan breaks down Amir's pricing model, clarifying unit prices and asking about enterprise tiers. Amir explains that Todoist for Business was a simple hack that unexpectedly generated over 30% of their revenue. | |
| Early Customer Traction and Team Expansion | 5 | 4 | 3 | 5 | Nathan presses Amir to recall early customer and headcount milestones. Amir explains their struggle around 2015 when scaling the engineering team and experimenting with flat hierarchies reduced productivity. | |
| Mobile-Driven Growth and Tracking Philosophy | 5 | 5 | 6 | 7 | Amir pushes back against traditional metric tracking, noting Doist does not celebrate revenue or user milestones. Nathan counters that tracking historical milestones is vital for documenting business case studies. | |
| Bootstrapping, Reinvestment, and Employee Stock Options | 5 | 3 | 5 | 3 | Amir details Doist's bootstrapped profitability and his decision to create a 25% employee equity pool. He explicitly rejects the Basecamp philosophy that equity in bootstrapped companies is valueless. | |
| Revenue Acceleration and the One Hundred Million Target | 6 | 4 | 4 | 6 | Amir shares his goal to scale from $15M to $100M ARR over five years. Nathan reacts with disbelief when Amir cannot recall the year they crossed $1M ARR, praising their 14x growth trajectory over four years. | |
| Consumer SaaS Dynamics and a Zen Philosophy on Churn | 7 | 5 | 6 | 7 | Nathan calculates an implied ~70% annual churn rate based on LTV and ARPU, questioning why Amir is not stressed about customer loss. Amir responds with a zen philosophy, accepting natural churn in consumer SaaS. | |
| Multiplayer Roadmap, Twist Revenue, and Resisting Acquisitions | 5 | 4 | 8 | 5 | Nathan inquires about acquisition interest, asking if Amir would accept a $200M all-cash buyout. Amir delivers an emphatic refusal, describing Doist as his life's work. | |
| The Famous Five Rapid-Fire Questions | 4 | 2 | 2 | 3 | Nathan leads Amir through the standard rapid-fire questions. Nathan redirects Amir when he recommends a podcast instead of naming a specific CEO. |
Statements from this episode (19)
Salihefendić monetized Todoist early by gating reminders to cover servers
“On the first year, actually, like, in the first couple of months, because, like, I was doing this on the side, and I didn't want to pay for the, like, server costs, so I just, like, you know, let's just make reminders a paid feature.”
Salihefendić: Todoist has hundreds of thousands of customers and $100 LTV
“We have like hundreds of thousands of customers and most of them pay like, you know, the lifetime value is like I would say about like a hundred or something like that.”
Todoist for Business drives 30% of revenue despite lacking improvements
“We basically created this, like, I think we spent three months, and it basically had generated, like, 30% or more of our revenues for many years now, and we have not really improved it.”
Todoist's low launch price anchored the entire to-do app market
“I said this initially, like very low price point and basically all the other competitors compete this or like, so I kind of like, because we were like one of the first online to do apps and we basically set the price point and everybody's kind of have the same…”
Bootstrapped Doist employs 90 people with zero salespeople
“So right now, like we are about I think, 85 people, maybe 90 because we are hiring more now. Initially most are engineers, like probably 50 engineers. We don't have any salespeople, so”
Adding headcount reduced Doist's productivity due to lacking organizational structure
“I mean, we basically hired more people and we didn't really become more productive. We actually became less productive because we didn't really have the structure in place to actually make people productive.”
Salihefendić warns against operating a company with no hierarchy
“So like, we also had like you know like I love affair with like no hierarchy and that didn't like, don't try that. Like it's not. Yeah. It didn't work that well.”
Doist historically ignored metrics and refuses to celebrate ARR milestones
“The thing to note is, like, we never actually celebrated any of the milestones so even right now, like, when you pass, like, one million or ten million in ARR, like, it's kind of, like, not really something that we celebrate a lot, and the same thing, like, wi…”
Salihefendić: Doist has never raised outside capital
“We didn't raise any money and we still have not raised any money.”
Salihefendić: Doist has been profitable for nearly all years
“I mean, we have actually been profitable like from like more all the years.”
Doist is establishing a 25% employee stock option pool
“Like we are actually like rolling out the like employee stock options right now, but like I own most of it and the employees will own in the end, I think, 25%.”
Salihefendić claims Basecamp is wrong about equity in bootstrapped startups
“I mean, honestly, like, I think I mean, I was kind of, like, against this, you know, like, the bootstrapping, especially, like, if you, like, hear the base camp guys, like, equity has no value and stuff like that, but it's kind of bullshit, because, like, equi…”
Salihefendić predicts Doist will surpass $100M annual revenue by 2025
“We want to pass like a hundred million in revenues in the next five years, or like, it's right now probably more like four and a half years.”
Doist projected passing $15M revenue in 2020 and $20M in 2021
“Yeah, I mean I think, like, this year we'll probably pass 15 and maybe a bit more if we are lucky, and next year I think we'll definitely pass, like, 20. That's at least the plan.”
Salihefendić: Doist closed 2019 with around $10M in revenue
“I think it's about yeah, I'm actually not a hundred percent, but probably around 10.”
Salihefendić ignores Doist's poor customer churn compared to SaaS benchmarks
“I mean, I know that the churn is bad, like compared to the benchmark, but honestly, like, I don't really care that much. Like there's some people inside a company that care more about this than me.”
Building productivity software for individual users makes user retention brutal
“Creating a tool that is mostly for individuals is brutal. Like, If you're doing anything, like, that's not something I can recommend doing, because you have, like, very hard time to actually keep users because you don't have, like, a natural way to bring them …”